Triethylamine → 4-Nitrophenylthiol acetate

HRID 905922Notes

Reaction equation

HRID 905922 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][C:7](O)=O.C(N(CC)CC)C.[N+:17](C1C=CC(CBr)=CC=1)([O-:19])=[O:18].C1C[O:31][CH2:30][CH2:29]1.C1(C)C=CC=CC=1>C1(C)C=CC=CC=1>[CH3:29][C:30]([S:1][C:5]1[CH:4]=[CH:3][C:2]([N+:17]([O-:19])=[O:18])=[CH:6][CH:7]=1)=[O:31]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 159702-Thiopheneacetic acidHCID 660114-Nitrobenzyl bromideHCID 22635083Tetrahydrofuran toluene

Product 1

HCID 270504-Nitrophenylthiol acetateYield 96%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To the solution of 5 ml (69.95 mmol) of thiolacetic acid and 12 ml of triethyl amine in 75 ml of toluene was added dropwise 7.5 g (34.71 mmol) of 4-nitrobenzyl bromide in 100 ml of 1:2 THF/Toluene for 4 hours. The mixture was continuously stirred overnight, evaporated and crystallized with EtAc/Toluene/Hexane to afford 7.1 g (96%) of the title compound. 1H NMR (CDCl3) 8.13 (ddd, 2H, J=2.5, 4.5, 9.3 Hz), 7.44 (ddd, 2H, J=2.5, 4.5, 9.3 Hz), 4.14 (s, 2H), 2.35 (S, 3H); 13C NMR 194.53, 145.73, 129.91, 124.07, 32.93, 30.50; MS M+234.34 (M+Na).

Workup

  1. customevaporated
  2. customcrystallized with EtAc/Toluene/Hexane

Sources & evidence

ORD record
ord-43338328c9384a198531987f94241a78
Source dataset
uspto-grants-2011_09
Patent number
US08012978B2

Reaction notes

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